WATER SOLUBLE GROUP IA AND IIA DOUBLE METAL SALT OF(-)- HYDROXYCITRIC ACID

SEL DOUBLE SOLUBLE DE METAUX DES GROUPES IA ET IIA D'ACIDE (-) HYDROXYCITRIQUE

English Abstract

This invention relates to a water soluble group IA and group IIA double metal
salt of (-)-hydroxycitric acid having the general formula I:
(see formula I)
The present invention is also directed to a process for preparing the water
soluble group IA and IIA double metal salt of (-)-hydroxycitric acid, and the
use
thereof in beverages and other food products.

French Abstract

L'invention concerne un nouveau sel double soluble de métaux des groupes IA et IIA d'acide (-)hydroxycitrique représenté par les formules générales (I) et plus particulièrement (II). L'invention concerne également un procédé permettant de préparer le sel double soluble de métaux des groupes IA et IIA d'acide (-)hydroxycitrique représenté par la formule générale (I). Ce procédé consiste à préparer un concentré liquide d'acide (-)hydroxycitrique ou une lactone solide de ce dernier à partir d'un extrait de Garcinia, à neutraliser l'acide (-)hydroxycitrique libre présent dans ce concentré liquide/lactone solide d'acide (-)hydroxycitrique à l'aide d'hydroxydes métalliques du groupe IA, à déplacer partiellement les ions métalliques du groupe IA dans les solutions salines ci-dessus par l'adjonction de chlorures métalliques du groupe IIA afin de former un sel double soluble de métaux des groupes IA et IIA d'acide (-)hydroxycitrique, puis à précipiter ce sel double métallique. L'invention concerne en outre l'utilisation de ce sel double métallique soluble d'acide (-)hydroxycitrique dans des boissons et d'autres produits alimentaires.

Claims

Claims:
1. A water soluble group IA and lIA double metal salt of (-)- hydroxycitric
acid (HCA) of
general formula I as given below:
<IMG>
where X+ is a IA group metal ion selected from the group consisting of Li+,
Na+, K+, Rb+,
Cs+, and Fr+;
where Y++ is IIA group metal selected from the group consisting of Be, Mg, Ca,
Sr, Ba,
and Ra;
where the concentration of X+ in the salt varies from 1.5-51.0% weight/weight,
the
concentration of Y++ in the salt varies from 2,0-50.9% weight/weight, and the
concentration of HCA in the salt varies from 31.0-93.0% weight/weight
depending on the
nature of X+ and Y++.
2. The water soluble group IA and IlA double metal salt of (-)-hydroxycitric
acid as claimed
in claim 1, wherein X+ is Na+ and Y++ is Ca++;
the concentration of sodium in the salt is 8.58% weight/weight;
the concentration of calcium in the salt is 14.92% weight/weight; and
the concentration of (-)-hydroxycitric acid is 76.50% weight/weight.
3. A process of preparing the water soluble group IA and IIA double metal salt
of (-)-
hydroxycitric acid as defined in claim 1 characterized by:
(i) preparing (-)-hydroxycitric acid liquid concentrate and/or solid lactone
of (-)-
hydroxycitric acid from Garcinia extract;
(ii) neutralizing the free (-)-hydroxycitric acid present in said (-)-
hydroxycitric acid
liquid concentrate and/or solid lactone of (-)-hydroxycitric acid with group
IA
metal hydroxides;
(iii) partially displacing the group IA metal ions by adding one equivalent of
a group
IIA metal chloride to form the water soluble group IA and IIA double metal
salt of
(-)-hydroxycitric acid; and
11

(iv) precipitating said group IA and IIA double metal salt of (-)-
hydroxycitric acid by
adding an aqueous polar solvent to obtain the group IA and IIA double metal
salt
of (-)-hydroxycitric acid, wherein said aqueous polar solvent is methanol,
ethanol,
propanol, isopropanol, or acetone.
4. The process as defined in claim 3 characterized in that the water soluble
group IA and
IIA double metal salt of (-)-hydroxycitric acid is obtained in powder form by
spray drying
prior to the solvent addition or spray drying the water solubilised solvent in
the
precipitate.
5. The process as defined in claim 3 characterized in that the preparation of
(-)-
hydroxycitric acid (HCA) concentrate from the Garcinia extract comprises:
(a) treating said Garcinia extract with a group IA metal hydroxide to obtain a
water
soluble group IA metal salt of (-)-hydroxycitric acid;
(b) displacing completely said group IA metal with group IIA metal by adding a
group
IIA metal chloride solution to precipitate a water insoluble group IIA metal
salt of
(-)-hydroxycitric acid;
(c) collecting said precipitate of group IIA metal salt of (-)-hydroxycitric
acid and
washing it with water;
(d) releasing (-)-hydroxycitric acid (HCA) by adding a water soluble organic
acid to
said precipitated group IIA metal salt of hydroxycitric acid (HCA) thereby
forming
a group IIA metal salt of said water soluble organic acid, wherein said water
soluble organic acid is oxalic acid;
(e) repeating the steps (c) and (d) to form a concentrate of (-)-hydroxycitric
acid; and
(f) optionally, decolorizing said (-)-hydroxycitric acid concentrate.
6. The process as defined in claim 3 characterized in that the preparation of
(-)-
hydroxycitric acid concentrate from the Garcinia extract comprises:
(a) extracting Garcinia rind with an aqueous polar solvent and filtering,
wherein said
aqueous polar solvent is 80% acetone in water:
(b) heating the filtrate under vacuum at 50-90°C to evaporate said
polar solvent;
(c) removing any water insoluble substances to get the (-)-hydroxycitric acid
concentrate; and
(d) optionally, decolorizing said (-)-hydroxycitric acid concentrate,
12

7. The process as defined in claim 3 characterized in that the preparation of
(-)-
hydroxycitric acid concentrate from the Garcinia extract comprises:
(a) loading the Garcinia extract containing free (-)-hydroxycitric acid on an
anion
exchange resin column;
(b) washing said column with a group IA metal hydroxide solution to get a
group IA
metal salt solution of (-)-hydroxycitric acid;
(c) loading said group IA metal salt solution of (-)-hydroxycitric acid on a
cation
exchange resin to get free (-)-hydroxycitric acid;
(d) heating said free (-)-hydroxycitric acid under vacuum to evaporate water
and get
(-)-hydroxycitric acid concentrate; and
(e) optionally, decolorizing said (-)-hydroxycitric acid concentrate by
heating with 2-
5% activated charcoal.
8. The process as defined in claim 3 comprising:
(a) loading the Garcinia extract containing free (-)-hydroxycitric acid on an
anion
exchange resin column;
(b) washing said anion exchange resin column with a group IA metal hydroxide
solution to obtain a group IA metal salt of (-)-hydroxycitric acid solution;
and
(c) treating said solution of a group IA metal salt of (-)-hydroxycitric acid
partially with
group IlA metal chloride to get a soluble group IIA metal salt of
hydroxycitric acid.
9. The process as defined in claim 3 characterized in that the solid lactone
of (-)-
hydroxycitric acid is prepared by:
(a) heating the (-)-hydroxycitric acid concentrate at 67°C to form a
syrup of (-)-
hydroxycitric acid lactone; and
(b) drying and desiccating said syrup to get a solid (-)-hydroxycitric acid
lactone.
10. The process as defined in claim 3 characterized in that the free
(-)-hydroxycitric acid present in step (ii) is neutralized by three
equivalents of group IA
metal hydroxides
11. The process as defined in any one of claims 3 to 9 characterized in that
the (-)-
hydroxycitric acid concentrate is decolorized by heating with 2-5% activated
charcoal.
13

12, The process as defined in claim 3 characterized in that the group IIA
metal chloride of
step (iii) is calcium chloride.
13. The process as defined in any one of claims 3 to 9 characterized in that
the group IA
metal hydroxides are selected from the group consisting of LiOH, NaOH, RbOH,
CsOH,
and FrOH, and the group IIA metal chlorides are selected from the group
consisting of
BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, and RaCl2.
14. The process as defined in claim 3 characterized in that the polar solvent
of step (iv) is
ethanol.
15. The process as defined in any one of claims 3 to 14 characterized in that
the soluble
group IA and IIA metal salt of (-)-hydroxycitric acid is the soluble sodium
and calcium
double salt of (-)-hydroxycitric acid.
16. A beverage containing 0-15 weight % alcohol and a syrup comprising a water
soluble
group IA and IIA double metal salt of (-)-hydroxycitric acid, as defined in
claim 1, in the
proportion 0.01% w/v -10 % w/v.
17. The beverage as defined in claim 16 characterized in that said beverage is
a beer
selected from the group consisting of a Pilsner beer having an alcohol content
of 3.0
weight %-3.9 weight %, a Dortmund beer having an alcohol content of 2.5 weight
%-4.0
weight %, a Munich beer having an alcohol content of 2.5 weight %-5.0 weight
%, a
Munich Ale having an alcohol content of 5.0 weight %-6.5 weight %, and a
Porter beer
having an alcohol content of 5.0 weight %-6.5 weight %, wherein the beer
comprises the
soluble double metal salt of group IA and IIA in the proportion 0,01%o w/v-0.5
% w/v.
18. The beverage as defined in claim 16 characterized in that said beverage is
an aerated or
non-aerated beverage or cola, and the syrup is either processed or naturally
occurring.
19. The beverage according to claim 18 wherein the syrup is honey.
14

Description

CA 02364245 2008-10-03
8991(PCT)
Water Soluble Group IA and HA Double Metal Salt of (-)- Hydroxycitric Acid
Technical field
This invention relates to a new soluble double metal salt of group IA and II
A of (-) hydroxycitric acid. process of preparing the same and its use in
beverages
and other food products without effecting their flavor and properties. This
product
with >98% purity can be used safely not only as a food supplement in various
nutriceutical formulations and beverages but also for effecting obesity
control.
Background Art
(-} Hydroxycitric acid (HCA) occurs in the fruit rind of Garcinia species (G.
to Cambogia, G. hidica and G. atrovh*iis). The first two species grow
abundantly in
India and the third occurs mostly in South East Asian countries. The success
of this
natural food product derived from Garcinia fruit has been documented and been
in
use since several centuries BC. Also known as "Kokum", the extracts of the
fruit
have been used, as a tart flavoring in meat and seafood dishes, turned into a
refreshing beverage that serves as a unique flavor enhancer, gourmet spice and
a
digestive after aheavy meal. In Aynuveda, the traditional ancient system of
herbal
medicine in India, Garrcmia is also considered to be one of the prime herbs
that are
beneficial for the heart.
In more recent tines, Gannia has received worldwide attention as a
10 nutriceutical for.effective obesity control. Several scientists including
at Hoffman-
La Roche have established that HCA, the active ingredient in the fruit,
prevents the
conversion of excess carbohydrates to fat in animals. The energy released by
the
excess carbohydrate is converted into and stored as glycogen, a readily usable
form
of energy. Interestingly, it has been shown to inhibit ATP dependent citrate,-
lyase,
a key enzyme in' diverting carbohydrate to fatty acids and cholesterol
synthesis.
(Sullivan et al. Lipids, 9:121 and 129 (1973). Sergio, W.. Medical Hypothesis
:7:39 (1988).
The age-old practice of consuming Garcinia rind as a food additive by
inhabitants of Malabar and Konkan coast of the Indian peninsula has
established
..._._..._ ................... .... ..... -. ...... _......... ..... .

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the safety of HCA. The isolation and chemical nature of (-) hydroxycitric acic
from Garcinia rind are described in the publication of Lewis Y.S., el aL
(Methods
in Enzymology, 13:613 (1967) and in the patents (Indian patents 160753 &
178298
and US patents 5536516 & 5656314).
s It is believed that consumption of HCA influences the body metabolism
leading to the saturation of glycogen receptors in the liver and a consequent
transmission of signals of satiation to brain. Even as a food supplement, (-)
HCA
helps a person to loselcontrol weight in a natural way without affecting
normal
physical activities.
to In view of its unique property, several health care formulations
incorporating HCA are being sold across the counter in the Western markets.
These include tablets, capsules, herbal teas, chocolate bars, milk shakes and
other
beverages. The active ingredient (HCA) from this insoluble HCA salt is
released
upon contact with hydrochloric and in the stomach and absorbed through the
is intestine to exert its metabolic effect
There is prior art on the preparation of a soluble tri-potassium- salt of (-)
HCA (Lewis Y.S., et al (Methods in Enzymology, 13:613 (1967), International
Patent application WO 96136585. However, its alkaline nature
and risks associated with the consumption of high potassium (-36%) makes this
io product unsuitable for HCA-based formulations.
In our earlier patents (Indian patent No. 178298 & US patents 5536516,
5656314) which describes preparation of a concentrate of (-) hydroxycitric
acid
and its lactone in liquid form, comprising of several steps like water
extraction of
Garcinia rind containing (-) hydroxycitric acid and its concentration, acetone
~s refinement of this concentrated water extract, evaporation of acetone.
loading thus
obtained refined extract on ion-exchange columns containing an anion exchange
resin followed by a cation exchange resin, and finally evaporation of the free
acid
liberated from the ion-exchange process to said concentration. This liquid
fonn of
(-) hvdroxycitric acid has problems of stability and half-life.

CA 02364245 2008-10-03
In addition, its highly acidic nature poses problems in formulating into
beverage and various other food products without affecting their flavor and
properties.
Disclosure of the Invention
The object of this invention is to overcome the above drawbacks by
developing a new soluble double metal salt of (-) hydroxycitric acid which
will
not pose any problem in formulating with beverages and various other food
products without affecting their flavor and properties.
To achieve the.said objective, this invention provides a new soluble double
to metal salt of group IA and 11 A of (-) hydroxycitric acid of general
formula I
and more particularly formula 11 as given below:
H
H H-C-COO' 1Vb*
H-=
c-coo x+ HO- C-coo,
HO-C-COO' HO-C-Coo I c~..
HO-C-coo- Y H
Formula I Formula 11
where X is IA group metal: Li or Na or K or Rb or Cs or Fr
where Y is 1IA group meta(: Be or Mg or Ca or Sr or Ba or Ra
where concentration of X in the salt varies from 1.5 - 5 1.0%,
the concentration of Y in the salts varies from 2.0 - 50.9%,
the concentration of (-)-hydroxycitric acid (HCA) in the salts varies from
31.0 -
93. 0% depending on the nature of X and Y.
concentration of sodium in the salt: 8.58%,
concentration of calcium in the salt: 14.92%
concentration of (-)-hydroxycitric acid: 76.50%,
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ENDED PAG
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This invention further relates to a process for preparing the said soluble
metal salt of group IA and IIA of (-) hydroxycitric acid of general formula I
or
more particularly formula II comprising:
Step 1: preparing (-) hydroxycitric acid liquid concentrate/solid lactone of
hydroxycitric acid from Garcinia extract,
Step 2: neutralizing the free (-) hydroxycitric acid present in the said
hydroxycitric acid liquid . concentrate/solid lactone present (-)
io hydroxycitric acid with group IA metal hydroxides
Step 3: displacing partially group IA metal ions in the above salt solutions
by
adding group IIA metal chlorides to form soluble double metal salt of
group IA and RA of (-) hydroxycitric acid,
Step 4: precipitating the said solubilised group IA and HA double metal salt
of
is (-) hydroxycitric acid by adding aqueous polar solvent to get soluble
double metal salt of group IA and IIA of (-) hydroxycitric acid.
The free (-) hydroxycitric acid present in the step 2 is neutralized by three
equivalents of group IA metal hydroxides.
Partial displacement of group IA metal ion in step 3 is carried out with one
20 equivalent of group IIA metal chloride.
The soluble double metal salt of group I A and IIA of (-) hydroxycitric acid
is obtained in powder from by spray drying prior to the solvent addition or
spray
drying water solubilised solvent precipitated material.
The said polar solvents are methanol, ethanol, propanol, isopropanol and
25 acetone.
The (-) hydroxycitric acid concentrate in step I is prepared from the
Garcinia extract by:
i) treating the said Garcinia extract with group IA metal hydroxide to obtain
soluble group IA metal salt of (-) hydroxycitric acid,
4.
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8991(PCT)
ii) displacing completely the said group IA metal ions with group IIA metal
ion
by adding group IIA metal chlorides solution to precipitate insoluble group
IIA metal salts of (-) hydroxycitric acid.
iii) collecting the said precipitate of insoluble group IIA metal salt of (-)
hydroxycitric acid and washing it with water,
iv) adding a water soluble organic acid to the said precipitated insoluble
group
II A metal salt of HCA to form a stronger salt of group IIA metal and release
(-) hydroxycitric acid,
v) repeating the steps (iii) and (iv) to form concentrate of (-) hydroxycitric
acid,
to vi) decolorizing the said (-) hydroxycitric acid concentrate, if desired.
The water soluble organic acid used in step (iv) is an oxalic acid.
The (-) hydroxycitric acid concentrate in step 1 is also prepared from the
Garcinia by:
i) extracting Garcinia rind with aqueous polar solvent and filtering,
ii) heating the filtrate in vacuum at 50-80 C to evaporate the said polar
solvent,
iii) removing the water insoluble substances to get the (-) hydroxycitric acid
concentrate,
iv) decolorizing the said (-) hydroxycitric acid concentrate, if necessary.
The aqueous polar solvent used in step 1 is 80% acetone in water.
The (-) hydroxycitric acid concentrate in step I is also prepared from the
Garcinia extract by:
i) loading the Garcinia extract containing free (-) hydroxycitric acid on
anion
exchange resin column,
ii) washing the said column with group IA metal hydroxide solution to get
group
,S IA metal salt of (-) hvdroxycitric acid,
iii) loading the said group IA metal salt solution of (-) hydroxycitric acid
on
cation exchange resin to get tree (-) hvdroxvvcitric acid,
iv) heating the said free (-) hvdroxvcitric acid in vacuum to evaporate water
and
get the (-) hvdroxycitric acid concentrate.
S

KMENDED PAG IN 009900004
23-02-2001
i) decolorizing the said (-) hydroxycitric acid concentrate, if necessary.
The said (-) hydroxycitric acid concentrate is decolorized by heating with 2-
5% activated charcoal, if desired.
The said lactone of (-) hydroxycitric acid in step 1 is prepared by:
i) heating the (-) hydroxycitric acid concentrate at 67 C to form syrup of (-
)
hydroxycitric acid lactone,
ii) drying and desiccating the said syrup to get solid mass of (-)
hydroxycitric
acid lactone.
A process for the preparation of soluble double metal salt of group IA and I1A
of (-) hydroxycitric acid comprising:
i) loading Garcinia extract containing free (-) hydroxycitric acid on an anion
exchange resin column,
ii) washing the said anion exchange resin column with Group IA metal
hydroxide to obtain group IA metal salt of (-) hydroxycitric acid solution.
iii) treating the said group IA metal salt of (-) hydroxycitric acid partially
with
group HA metal chloride to get soluble double metal salt of group 1A and I1A
of (-) hydroxycitric acid.
Group IA metal hydroxides used are LiOH, NaOH, KOH, RbOH, CsOH and
FrOH.
Group HA metal chlorides BeC12, MgCl2, CaC12, Sr(-'12, BaCl2 and RaC12.
The soluble double metal salt of group IA and IIA of (-) hydroxycitric acid is
soluble sodium and calcium double metal salt of (-) hydroxycitric acid.
The process will now be described with reference to the following examples.
Example 1:
Water extract of Garcinia rind is obtained by counter current extraction, this
is
carried out in three vessels more specifically each time fresh Garcinia rind
each
time 1 Kg is loaded into vessel 3 and treated with 1.5 liters of water, the
rind is
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23-02-2001
moved from V3 to V2 then to V1. On the other hand the extract was moved from
V1 to V2 then to V3. The extract obtained starting from 3Kgs of rind was 3.6
litres
containing 620gms of acid along with the other water-soluble substances. The
total
soluble constituents in the extract i.e. brix was found to be 43 degrees. The
extraction
efficiency was found to be 90%. This acid was transferred to a vessel and
neutralized by
addition if 358 gm of sodium hydroxide. After cooling this solution to room
temperature,
500 ml of solution containing 490 gin of calcium chloride was added to it and
resultant
insoluble calcium salt was centrifuged and washed thoroughly to removed the
color and
wo water soluble impurities. The salt obtained was dried and weight is found
to be 693
gm.One hundred grams of this insoluble salt was taken in a one liter vessel to
and 71.32
gin oxalic acid dihydrate dissolved in 350 ml of water was added and stirred
at 150 RPM
on a shaker for 30 min, and the supernatant 210 ml of was collected. To this
supernatant
71.32 gm of oxalic acid dihydrate was added and another 100 gm of calcium
hydroxycitrate added and this procedure is followed until the hydroxycitric
acid content
in the extract reaches -45% detected by high performance liquid chromatography
(HPLC). The traces of oxalic acid were also removed by finally adding excess
calcium
hydroxycitrate. This was monitored by HPLC by observing the total absence of
oxalic
acid peak. The solution of hydroxycitric acid thus obtained was found to
contain 202 gm
of acid in 450 ml of extract. This was neutralized by 117 gm of sodium
hydroxide and the
solution was cooled to room temperature. To this sodium salt solution of
hydroxycitric
acid, 200 ml of solution containing 81 gm of calcium chloride was added drop
wise with
vigorous stirring. The soluble sodium and calcium double metal salt of
hydroxycitric acid
was then precipitated by addition of ethanol. Then precipitated salt was
filtered, washed
with ethanol and dried to obtain 234 gin of the soluble sodium and calcium
double metal
salt of hydroxycitric acid (yield: 91.2%). In another experiment, the above
procedure was
repeated exactly after collecting the ethanol precipitated material. This was
again
dissolved in water
1
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to 30% and the material thus obtained was spray dried to obtain 243 gm of the
soluble salt of hydroxycitric acid (yield 95%).
EXAMPLE 2:
One hundred gm Garcinia Cambogia rind was extracted 4 times with 80%
acetone in water (250 ml each time) for 4 hours. The combined extract (830-ml)
was
concentrated to 300 ml by heating in vacuo at 56 C (500 millibar and filtered
through
cheese cloth to remove water insoluble non polar substances. The filtrate (260-
m1)
containing 18 gm of hydroxycitric acid decolorized by addition of 2.6 gm of
activated
io charcoal and filtered The resultant clear solution was concentrated to 50
ml, and the
free acid was converted into the sodium salt of hydroxycitric acid by the
addition of
i l gm of sodium hydroxide pellets, were added. To this formed solution of
sodium
salt of (-) hydroxycitric acid 20 ml of solution containing 9 gm of calcium
chloride
was added drop wise with vigorous stirring. The soluble sodium and calcium
double
metal salt of hydroxycitric acid is then precipitated by addition of ethanol.
The
precipitated soluble sodium and calcium double metal salt is filtered, washed
with
ethanol and dried to obtain 20.7 gm of the soluble sodium and calcium double
metal
salt of hydroxycitric acid (yield 89.84%).
EXAMPLE 3: An anion exchange resin (bed volume IL) was loaded onto a glass
column and washed thoroughly with 10% aqueous sodium hydroxide to remove the
chloride present in the resin. The column was then washed with water till the
eluate
pH was neutral. Three hundred milliliters of an aqueous solution containing
108 gm
of (-) hydroxycitric acid was loaded onto the column and washed with water to
remove the colored materials. The column was eluted with I liter of an aqueous
solution containing 63 gm of sodium hydroxide followed by 0.5 L of water. The
combined eluate (1.5 liters) containing sodium salt of hydroxycitric acid was
divided
into two parts (750 ml each) and the soluble sodium and calcium double metal
salt
was prepared as follows. A portion of the sodium salt of hydroxycitric acid
(750 ml)
was concentrated to 200 ml. Fifty milliliters of a solution containing 20.25
gm of
calcium chloride was
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CA 02364245 2008-10-03
added drop wise with vigorous stirring. The soluble salt of hydroxycitric acid
thus formed was precipitated by the addition of ethanol, collected by
filtration, washed. with ethanol and dried to obtain 60.3 gm of the soluble
calcium salt of hydroxycitric acid (yield: 91.8%).
b) The remaining portion of the eluate (750-m1) from the anion exchange
column was passed through a column of cation exchange resin (bed
volume 750ml). The column was washed with water until the pH of the
eluent reached neutral. One liter of the flow through which contained 45
gm of free (-) hydroxycitric acid was collected, concentrated in Vacuo to
100 ml and.reneutralized by the addition of 27 gm of sodium hydroxide
pellets. To the resultant solution of the sodium salt of (-) hydroxycitric
acid, 50 ml of a solution containing 18 gm of calcium chloride was added
drop wise with vigorous stirring. The resultant soluble calcium salt of
hydroxycitric acid was precipitated by the addition of ethanol. The
precipitated salt was filtered, washed with ethanol and dried to obtain
54 gm of the soluble calcium salt of (-) hydroxycitric acid (yield:
93.75%).
EXAMPLE 4:
One hundred milliliters of 48% enriched aqueous solution of hydroxycitric
acid solution was evaporated 67 C in vacuo to remove water. The syrup thus
formed was transferred into Petri dishes dried and desiccated under vacuum
for 4-5 hours. The solid lactone of hydroxycitric acid weighing 30.6 gm was
collected. To the said Lactone residue, 60 ml of a solution containing 18 gm
of
sodium hydroxide was added. To the resultant solution of the sodium salt of (-
)
hydroxycitric acid, 30 ml of a solution containing 12.6 gm of calcium chloride
was added drop wise with vigorous stirring. The soluble salt of hydroxycitric
acid is then precipitated by addition of ethanol. The precipitated salt was
filtered, washed with ethanol and dried to obtain 36 gm of the soluble calcium
salt of hydroxycitric acid (yield: 9.91%).
9

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899 t(PCT)
This invention also provides the use of the said soluble double metal salt of
group IA and IIA of (-) hydroxycitric acid of formula I and particularly,
formula 11
in beverages and other food products.
Beverages containing 0-15 weight % alcohol and syrups including soluble
double metal salt of group IA and IIA of (-) hydroxycitric acid of formula I
or
formula II in the proportion 0.01 -10 % w/v.
The said beverage is a Pilsner beer containing alcohol content 3.0-3.8
weight % or Dortmund beer containing alcohol content 2.5-4.0 weight % or
Munich beer containing alcohol content 2.0-5.0 weight % or Munich Ale or
io Porter beer containing alcohol contents 2.0-5.0 weight % or Stout beer
containing
alcohol content 5.0-6.5 weight %, each said beer includes the soluble double
metal
salt of group IA or IIA of formula I or 11 in the proportion 0.01-0.5 % w/v.
The said beverage is aerated or non-aerated beverage/colas and the syrups
are either processed or naturally occurring like honey including soluble
double
metal salt of group IA and IIA of (-) hydroxycitric acid of formula I or II in
the
proportion 0.01-10 % w/v.
Soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of
formula I or formula II in the proportion 0.01-10 % w/v is added at any stage
during the production of the beverage or processed syrups.
?S

Representative Drawing